# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xxx
_database_code_depnum_ccdc_archive 'CCDC 1056575'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N3 O5 P'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C19 H20 N3 O5 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         401.35
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   14.390(3)
_cell_length_b                   9.5870(16)
_cell_length_c                   14.773(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.651(2)
_cell_angle_gamma                90
_cell_volume                     1942.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2695
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.310
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.947

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            12702
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3517
_reflns_number_gt                3020
_reflns_threshold_expression     >2sigma(I)


_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988


_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  "PLATON (Spek, 2003)'"
#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.4382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3517
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


_refine_diff_density_max         0.307
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.041

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P Uani 0.32253(3) 0.36749(5) 0.99456(3) 1.000 0.0366(2) . .
O1 O Uani 0.52470(9) 0.09022(15) 0.90680(10) 1.000 0.0533(5) . .
O2 O Uani -0.07828(9) -0.08669(18) 0.84877(11) 1.000 0.0627(5) . .
O3 O Uani 0.21535(9) 0.41202(16) 0.98516(10) 1.000 0.0567(5) . .
O4 O Uani 0.37575(12) 0.49768(15) 0.97236(10) 1.000 0.0607(5) . .
O5 O Uani 0.36453(10) 0.30385(15) 1.08824(8) 1.000 0.0522(5) . .
N1 N Uani 0.46938(11) -0.12660(17) 0.84967(11) 1.000 0.0483(5) . .
N2 N Uani 0.33176(12) 0.17490(16) 0.76798(10) 1.000 0.0442(5) . .
N3 N Uani 0.33299(10) 0.28933(15) 0.82230(10) 1.000 0.0401(4) . .
C1 C Uani 0.45981(12) 0.01074(19) 0.86541(11) 1.000 0.0391(5) . .
C2 C Uani 0.38191(14) -0.1858(2) 0.79453(12) 1.000 0.0446(6) . .
C3 C Uani 0.36529(19) -0.3219(2) 0.76259(15) 1.000 0.0635(8) . .
C4 C Uani 0.2728(2) -0.3545(3) 0.70568(16) 1.000 0.0734(9) . .
C5 C Uani 0.20038(19) -0.2564(3) 0.68143(16) 1.000 0.0708(9) . .
C6 C Uani 0.21685(15) -0.1192(3) 0.71430(13) 1.000 0.0566(7) . .
C7 C Uani 0.30838(12) -0.08499(19) 0.77291(11) 1.000 0.0409(5) . .
C8 C Uani 0.34956(12) 0.04725(18) 0.82405(11) 1.000 0.0354(5) . .
C9 C Uani 0.31216(11) 0.09197(17) 0.90963(10) 1.000 0.0338(5) . .
C10 C Uani 0.32396(11) 0.24927(18) 0.90277(11) 1.000 0.0347(5) . .
C11 C Uani 0.20827(12) 0.04896(18) 0.89881(11) 1.000 0.0356(5) . .
C12 C Uani 0.18920(13) -0.06494(19) 0.94729(12) 1.000 0.0420(5) . .
C13 C Uani 0.09479(13) -0.1131(2) 0.93357(13) 1.000 0.0472(6) . .
C14 C Uani 0.01732(12) -0.0468(2) 0.86937(13) 1.000 0.0455(6) . .
C15 C Uani 0.03508(13) 0.0697(2) 0.82058(13) 1.000 0.0472(6) . .
C16 C Uani 0.12881(12) 0.1168(2) 0.83560(12) 1.000 0.0417(6) . .
C17 C Uani -0.10149(16) -0.1953(3) 0.90327(17) 1.000 0.0647(8) . .
C18 C Uani 0.1577(2) 0.4898(3) 0.9027(2) 1.000 0.0936(11) . .
C19 C Uani 0.39858(19) 0.6169(3) 1.03587(19) 1.000 0.0739(9) . .
H1 H Uiso 0.52310 -0.17220 0.87110 1.000 0.0580 calc R
H2 H Uiso 0.32170 0.17740 0.70760 1.000 0.0530 calc R
H3 H Uiso 0.41450 -0.38860 0.77890 1.000 0.0760 calc R
H4 H Uiso 0.25930 -0.44520 0.68320 1.000 0.0880 calc R
H5 H Uiso 0.13890 -0.28160 0.64230 1.000 0.0850 calc R
H6 H Uiso 0.16750 -0.05290 0.69710 1.000 0.0680 calc R
H9 H Uiso 0.35610 0.05660 0.96960 1.000 0.0410 calc R
H12 H Uiso 0.24090 -0.11080 0.99040 1.000 0.0500 calc R
H13 H Uiso 0.08390 -0.18980 0.96750 1.000 0.0570 calc R
H15 H Uiso -0.01670 0.11570 0.77770 1.000 0.0570 calc R
H16 H Uiso 0.13960 0.19530 0.80310 1.000 0.0500 calc R
H17A H Uiso -0.17040 -0.21290 0.88120 1.000 0.0970 calc R
H17B H Uiso -0.08290 -0.16820 0.96890 1.000 0.0970 calc R
H17C H Uiso -0.06690 -0.27840 0.89670 1.000 0.0970 calc R
H18A H Uiso 0.09410 0.50770 0.90850 1.000 0.1400 calc R
H18B H Uiso 0.15140 0.43620 0.84620 1.000 0.1400 calc R
H18C H Uiso 0.18940 0.57670 0.89880 1.000 0.1400 calc R
H19A H Uiso 0.43110 0.68670 1.01000 1.000 0.1110 calc R
H19B H Uiso 0.44040 0.58800 1.09680 1.000 0.1110 calc R
H19C H Uiso 0.33940 0.65490 1.04280 1.000 0.1110 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.5654(15) . . yes
P1 O4 1.5506(17) . . yes
P1 O5 1.4648(13) . . yes
P1 C10 1.7722(17) . . yes
O1 C1 1.217(2) . . yes
O2 C14 1.370(2) . . yes
O2 C17 1.417(3) . . yes
O3 C18 1.454(3) . . yes
O4 C19 1.452(3) . . yes
N1 C1 1.351(2) . . yes
N1 C2 1.396(3) . . yes
N2 N3 1.356(2) . . yes
N2 C8 1.456(2) . . yes
N3 C10 1.293(2) . . yes
N1 H1 0.8600 . . no
N2 H2 0.8600 . . no
C1 C8 1.557(3) . . no
C2 C3 1.383(3) . . no
C2 C7 1.397(3) . . no
C3 C4 1.377(4) . . no
C4 C5 1.368(4) . . no
C5 C6 1.397(4) . . no
C6 C7 1.379(3) . . no
C7 C8 1.503(2) . . no
C8 C9 1.576(2) . . no
C9 C10 1.524(2) . . no
C9 C11 1.512(2) . . no
C11 C16 1.398(2) . . no
C11 C12 1.378(2) . . no
C12 C13 1.390(3) . . no
C13 C14 1.380(3) . . no
C14 C15 1.394(3) . . no
C15 C16 1.375(3) . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C9 H9 0.9800 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C15 H15 0.9300 . . no
C16 H16 0.9300 . . no
C17 H17A 0.9600 . . no
C17 H17B 0.9600 . . no
C17 H17C 0.9600 . . no
C18 H18A 0.9600 . . no
C18 H18B 0.9600 . . no
C18 H18C 0.9600 . . no
C19 H19A 0.9600 . . no
C19 H19B 0.9600 . . no
C19 H19C 0.9600 . . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 O4 107.35(9) . . . yes
O3 P1 O5 108.09(8) . . . yes
O3 P1 C10 110.26(8) . . . yes
O4 P1 O5 116.51(8) . . . yes
O4 P1 C10 103.41(8) . . . yes
O5 P1 C10 111.06(8) . . . yes
C14 O2 C17 118.21(17) . . . yes
P1 O3 C18 120.70(15) . . . yes
P1 O4 C19 121.77(15) . . . yes
C1 N1 C2 112.07(16) . . . yes
N3 N2 C8 112.01(13) . . . yes
N2 N3 C10 108.48(14) . . . yes
C1 N1 H1 124.00 . . . no
C2 N1 H1 124.00 . . . no
C8 N2 H2 124.00 . . . no
N3 N2 H2 124.00 . . . no
O1 C1 C8 126.28(16) . . . yes
N1 C1 C8 107.24(15) . . . yes
O1 C1 N1 126.44(17) . . . yes
N1 C2 C3 127.9(2) . . . yes
C3 C2 C7 122.28(19) . . . no
N1 C2 C7 109.80(16) . . . yes
C2 C3 C4 117.2(2) . . . no
C3 C4 C5 121.5(2) . . . no
C4 C5 C6 121.4(2) . . . no
C5 C6 C7 118.1(2) . . . no
C2 C7 C8 108.24(15) . . . no
C6 C7 C8 132.27(19) . . . no
C2 C7 C6 119.49(19) . . . no
C1 C8 C9 107.54(12) . . . no
C7 C8 C9 117.02(14) . . . no
N2 C8 C9 100.59(13) . . . yes
N2 C8 C1 113.24(15) . . . yes
N2 C8 C7 116.65(13) . . . yes
C1 C8 C7 101.96(14) . . . no
C8 C9 C10 98.27(12) . . . no
C8 C9 C11 114.09(13) . . . no
C10 C9 C11 112.91(14) . . . no
N3 C10 C9 113.54(14) . . . yes
P1 C10 N3 122.78(13) . . . yes
P1 C10 C9 123.67(11) . . . yes
C9 C11 C16 121.73(15) . . . no
C12 C11 C16 117.66(17) . . . no
C9 C11 C12 120.49(15) . . . no
C11 C12 C13 121.81(17) . . . no
C12 C13 C14 119.81(17) . . . no
O2 C14 C13 124.85(17) . . . yes
C13 C14 C15 119.19(17) . . . no
O2 C14 C15 115.97(17) . . . yes
C14 C15 C16 120.28(17) . . . no
C11 C16 C15 121.23(17) . . . no
C2 C3 H3 121.00 . . . no
C4 C3 H3 121.00 . . . no
C3 C4 H4 119.00 . . . no
C5 C4 H4 119.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 119.00 . . . no
C5 C6 H6 121.00 . . . no
C7 C6 H6 121.00 . . . no
C8 C9 H9 110.00 . . . no
C10 C9 H9 110.00 . . . no
C11 C9 H9 110.00 . . . no
C11 C12 H12 119.00 . . . no
C13 C12 H12 119.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C11 C16 H16 119.00 . . . no
C15 C16 H16 119.00 . . . no
O2 C17 H17A 109.00 . . . no
O2 C17 H17B 109.00 . . . no
O2 C17 H17C 109.00 . . . no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 109.00 . . . no
O3 C18 H18A 110.00 . . . no
O3 C18 H18B 109.00 . . . no
O3 C18 H18C 110.00 . . . no
H18A C18 H18B 109.00 . . . no
H18A C18 H18C 109.00 . . . no
H18B C18 H18C 109.00 . . . no
O4 C19 H19A 109.00 . . . no
O4 C19 H19B 109.00 . . . no
O4 C19 H19C 109.00 . . . no
H19A C19 H19B 109.00 . . . no
H19A C19 H19C 109.00 . . . no
H19B C19 H19C 110.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 P1 O3 C18 47.99(18) . . . . no
O5 P1 O3 C18 174.44(17) . . . . no
C10 P1 O3 C18 -63.99(18) . . . . no
O3 P1 O4 C19 69.01(19) . . . . no
O5 P1 O4 C19 -52.3(2) . . . . no
C10 P1 O4 C19 -174.41(17) . . . . no
O4 P1 C10 N3 -22.98(17) . . . . no
O5 P1 C10 N3 -148.68(15) . . . . no
O3 P1 C10 C9 -86.85(15) . . . . no
O4 P1 C10 C9 158.64(14) . . . . no
O5 P1 C10 C9 32.94(16) . . . . no
O3 P1 C10 N3 91.53(16) . . . . no
C17 O2 C14 C15 -173.61(19) . . . . no
C17 O2 C14 C13 6.4(3) . . . . no
C2 N1 C1 C8 6.11(19) . . . . no
C1 N1 C2 C3 178.12(19) . . . . no
C1 N1 C2 C7 -1.2(2) . . . . no
C2 N1 C1 O1 -175.99(17) . . . . no
C8 N2 N3 C10 -16.8(2) . . . . no
N3 N2 C8 C1 -88.17(18) . . . . no
N3 N2 C8 C9 26.29(18) . . . . no
N3 N2 C8 C7 153.94(15) . . . . no
N2 N3 C10 P1 179.80(13) . . . . no
N2 N3 C10 C9 -1.7(2) . . . . no
O1 C1 C8 N2 47.7(2) . . . . no
O1 C1 C8 C7 173.88(17) . . . . no
N1 C1 C8 C7 -8.20(17) . . . . no
N1 C1 C8 N2 -134.36(15) . . . . no
N1 C1 C8 C9 115.44(15) . . . . no
O1 C1 C8 C9 -62.5(2) . . . . no
N1 C2 C3 C4 -177.6(2) . . . . no
C7 C2 C3 C4 1.7(3) . . . . no
C3 C2 C7 C6 -3.0(3) . . . . no
N1 C2 C7 C8 -4.5(2) . . . . no
C3 C2 C7 C8 176.15(18) . . . . no
N1 C2 C7 C6 176.36(16) . . . . no
C2 C3 C4 C5 0.2(4) . . . . no
C3 C4 C5 C6 -0.8(4) . . . . no
C4 C5 C6 C7 -0.5(3) . . . . no
C5 C6 C7 C2 2.3(3) . . . . no
C5 C6 C7 C8 -176.56(19) . . . . no
C6 C7 C8 C9 69.5(2) . . . . no
C2 C7 C8 C1 7.53(17) . . . . no
C2 C7 C8 N2 131.42(17) . . . . no
C2 C7 C8 C9 -109.46(17) . . . . no
C6 C7 C8 C1 -173.48(19) . . . . no
C6 C7 C8 N2 -49.6(3) . . . . no
C1 C8 C9 C10 95.13(14) . . . . no
C1 C8 C9 C11 -145.14(14) . . . . no
N2 C8 C9 C11 96.16(16) . . . . no
C7 C8 C9 C11 -31.3(2) . . . . no
C7 C8 C9 C10 -150.97(14) . . . . no
N2 C8 C9 C10 -23.57(15) . . . . no
C8 C9 C10 N3 16.90(18) . . . . no
C8 C9 C11 C12 102.06(18) . . . . no
C8 C9 C11 C16 -73.9(2) . . . . no
C10 C9 C11 C12 -146.84(15) . . . . no
C10 C9 C11 C16 37.2(2) . . . . no
C8 C9 C10 P1 -164.59(12) . . . . no
C11 C9 C10 P1 74.80(16) . . . . no
C11 C9 C10 N3 -103.72(16) . . . . no
C9 C11 C16 C15 174.60(16) . . . . no
C12 C11 C16 C15 -1.5(3) . . . . no
C9 C11 C12 C13 -175.25(16) . . . . no
C16 C11 C12 C13 0.9(3) . . . . no
C11 C12 C13 C14 0.5(3) . . . . no
C12 C13 C14 C15 -1.3(3) . . . . no
C12 C13 C14 O2 178.66(18) . . . . no
O2 C14 C15 C16 -179.25(17) . . . . no
C13 C14 C15 C16 0.7(3) . . . . no
C14 C15 C16 C11 0.7(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
P1 H1 3.1200 . 3_657 no
P1 H2 3.1800 . 4_555 no
O1 N2 3.020(2) . . no
O1 C10 3.251(2) . . no
O1 C19 3.042(3) . 3_667 no
O3 C17 3.370(3) . 3_557 no
O4 N3 2.908(2) . . no
O5 N1 2.848(2) . 3_657 no
O5 N2 2.841(2) . 4_555 no
O1 H9 2.8700 . . no
O1 H19A 2.4500 . 3_667 no
O1 H9 2.5200 . 3_657 no
O2 H18B 2.7600 . 2_546 no
O2 H4 2.8500 . 2_556 no
O3 H19C 2.9000 . . no
O4 H18C 2.6800 . . no
O5 H1 1.9900 . 3_657 no
O5 H2 2.0400 . 4_555 no
N1 O5 2.848(2) . 3_657 no
N2 O1 3.020(2) . . no
N2 C16 3.407(3) . . no
N2 O5 2.841(2) . 4_554 no
N3 C16 3.429(2) . . no
N3 O4 2.908(2) . . no
N2 H17A 2.8800 . 2_556 no
N3 H16 2.8600 . . no
C6 C16 3.363(3) . . no
C6 C11 3.201(3) . . no
C7 C12 3.506(3) . . no
C7 C16 3.568(3) . . no
C10 O1 3.251(2) . . no
C11 C6 3.201(3) . . no
C12 C7 3.506(3) . . no
C16 N2 3.407(3) . . no
C16 C7 3.568(3) . . no
C16 C6 3.363(3) . . no
C16 N3 3.429(2) . . no
C17 O3 3.370(3) . 3_557 no
C19 O1 3.042(3) . 3_667 no
C1 H9 3.0800 . 3_657 no
C4 H12 3.0900 . 4_544 no
C10 H18B 2.9700 . . no
C10 H16 2.6700 . . no
C11 H6 3.0200 . . no
C13 H17B 3.0900 . 3_557 no
C13 H17C 2.7300 . . no
C13 H17B 2.8100 . . no
C14 H17B 3.0800 . 3_557 no
C15 H5 3.0700 . 2_556 no
C16 H18B 3.0800 . . no
C16 H6 2.8000 . . no
C17 H13 2.5500 . . no
C18 H15 3.0700 . 2_556 no
H1 P1 3.1200 . 3_657 no
H1 O5 1.9900 . 3_657 no
H2 H17A 2.4200 . 2_556 no
H2 P1 3.1800 . 4_554 no
H2 O5 2.0400 . 4_554 no
H4 O2 2.8500 . 2_546 no
H5 C15 3.0700 . 2_546 no
H5 H15 2.5900 . 2_546 no
H5 H13 2.4800 . 4_544 no
H6 C11 3.0200 . . no
H6 C16 2.8000 . . no
H9 O1 2.8700 . . no
H9 H12 2.3900 . . no
H9 O1 2.5200 . 3_657 no
H9 C1 3.0800 . 3_657 no
H12 H9 2.3900 . . no
H12 C4 3.0900 . 4_545 no
H13 C17 2.5500 . . no
H13 H17B 2.4200 . . no
H13 H17C 2.2700 . . no
H13 H5 2.4800 . 4_545 no
H15 C18 3.0700 . 2_546 no
H15 H5 2.5900 . 2_556 no
H16 N3 2.8600 . . no
H16 C10 2.6700 . . no
H16 H18B 2.3900 . . no
H17A N2 2.8800 . 2_546 no
H17A H2 2.4200 . 2_546 no
H17B C13 2.8100 . . no
H17B H13 2.4200 . . no
H17B C13 3.0900 . 3_557 no
H17B C14 3.0800 . 3_557 no
H17C C13 2.7300 . . no
H17C H13 2.2700 . . no
H18B C10 2.9700 . . no
H18B C16 3.0800 . . no
H18B H16 2.3900 . . no
H18B O2 2.7600 . 2_556 no
H18C O4 2.6800 . . no
H19A O1 2.4500 . 3_667 no
H19C O3 2.9000 . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O5 0.8600 1.9900 2.848(2) 171.00 3_657 yes
N2 H2 O5 0.8600 2.0400 2.841(2) 154.00 4_554 yes
C9 H9 O1 0.9800 2.5200 3.472(2) 163.00 3_657 yes
C19 H19A O1 0.9600 2.4500 3.042(3) 119.00 3_667 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xxx
_database_code_depnum_ccdc_archive 'CCDC 1056898'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 F N3 O5 P'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C19 H15 F N3 O5 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         415.31
_chemical_compound_source        'see text'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.955(2)
_cell_length_b                   9.519(2)
_cell_length_c                   12.242(3)
_cell_angle_alpha                90.177(3)
_cell_angle_beta                 94.210(3)
_cell_angle_gamma                116.002(4)
_cell_volume                     934.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1325
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.960

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'


_diffrn_reflns_number            6428
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3187
_reflns_number_gt                2646
_reflns_threshold_expression     >2sigma(I)


_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.924


_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  "PLATON (Spek, 2003)'"


#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0724P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3187
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.046

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P Uani 1.02013(6) 0.29549(6) 0.60278(4) 1.000 0.0322(2) . .
F1 F Uani 0.26902(19) 0.03953(16) 1.02709(11) 1.000 0.0603(5) . .
O1 O Uani 0.46998(19) -0.25502(16) 0.50801(12) 1.000 0.0456(5) . .
O2 O Uani 0.9373(2) 0.33315(19) 0.86140(12) 1.000 0.0496(5) . .
O3 O Uani 1.01679(18) 0.24729(16) 0.48034(11) 1.000 0.0410(5) . .
O4 O Uani 1.14795(19) 0.25235(18) 0.67028(13) 1.000 0.0476(5) . .
O5 O Uani 1.05856(19) 0.45884(16) 0.62662(13) 1.000 0.0456(5) . .
N1 N Uani 0.3303(2) -0.24558(19) 0.65390(14) 1.000 0.0348(5) . .
N2 N Uani 0.5849(2) -0.04056(17) 0.62845(12) 1.000 0.0302(5) . .
N3 N Uani 0.7258(2) 0.03019(18) 0.57603(13) 1.000 0.0330(5) . .
C1 C Uani 0.4581(2) -0.1897(2) 0.58930(15) 1.000 0.0319(6) . .
C2 C Uani 0.3158(3) -0.1713(2) 0.74841(15) 1.000 0.0323(6) . .
C3 C Uani 0.1767(3) -0.2462(2) 0.80723(18) 1.000 0.0427(7) . .
C4 C Uani 0.1602(3) -0.1744(3) 0.90061(17) 1.000 0.0456(7) . .
C5 C Uani 0.2850(3) -0.0290(2) 0.93381(16) 1.000 0.0412(7) . .
C6 C Uani 0.4239(3) 0.0471(2) 0.87958(15) 1.000 0.0371(6) . .
C7 C Uani 0.4410(2) -0.0240(2) 0.78381(15) 1.000 0.0298(6) . .
C8 C Uani 0.5826(2) 0.0435(2) 0.71945(14) 1.000 0.0298(6) . .
C9 C Uani 0.7328(2) 0.1769(2) 0.72630(14) 1.000 0.0300(6) . .
C10 C Uani 0.8164(2) 0.1620(2) 0.63636(15) 1.000 0.0306(6) . .
C11 C Uani 0.8063(2) 0.3081(2) 0.81139(14) 1.000 0.0328(6) . .
C12 C Uani 0.7194(3) 0.4071(2) 0.82885(15) 1.000 0.0337(6) . .
C13 C Uani 0.5979(3) 0.4087(2) 0.75184(17) 1.000 0.0428(7) . .
C14 C Uani 0.5258(3) 0.5088(3) 0.7683(2) 1.000 0.0559(9) . .
C15 C Uani 0.5741(3) 0.6063(3) 0.8606(3) 1.000 0.0647(10) . .
C16 C Uani 0.6915(4) 0.6028(3) 0.9387(2) 1.000 0.0601(9) . .
C17 C Uani 0.7649(3) 0.5042(3) 0.92292(18) 1.000 0.0450(7) . .
C18 C Uani 1.1641(3) 0.3307(3) 0.4218(2) 1.000 0.0556(8) . .
C19 C Uani 1.1438(4) 0.0996(3) 0.6591(3) 1.000 0.0723(11) . .
H1 H Uiso 0.246(3) -0.346(3) 0.6323(19) 1.000 0.054(7) . .
H3 H Uiso 0.09480 -0.34470 0.78360 1.000 0.0510 calc R
H4 H Uiso 0.06720 -0.22280 0.94020 1.000 0.0550 calc R
H6 H Uiso 0.50590 0.14440 0.90540 1.000 0.0440 calc R
H13 H Uiso 0.56510 0.34280 0.68950 1.000 0.0510 calc R
H14 H Uiso 0.44470 0.51010 0.71690 1.000 0.0670 calc R
H15 H Uiso 0.52730 0.67500 0.87030 1.000 0.0780 calc R
H16 H Uiso 0.72110 0.66670 1.00190 1.000 0.0720 calc R
H17 H Uiso 0.84490 0.50270 0.97520 1.000 0.0540 calc R
H18A H Uiso 1.14400 0.28810 0.34800 1.000 0.0830 calc R
H18B H Uiso 1.25680 0.31960 0.45810 1.000 0.0830 calc R
H18C H Uiso 1.18880 0.43950 0.42050 1.000 0.0830 calc R
H19A H Uiso 1.23150 0.09530 0.70690 1.000 0.1090 calc R
H19B H Uiso 1.15910 0.08060 0.58460 1.000 0.1090 calc R
H19C H Uiso 1.03810 0.02140 0.67830 1.000 0.1090 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.5605(15) . . yes
P1 O4 1.5611(19) . . yes
P1 O5 1.4611(15) . . yes
P1 C10 1.787(2) . . yes
F1 C5 1.361(3) . . yes
O1 C1 1.208(2) . . yes
O2 C11 1.207(3) . . yes
O3 C18 1.452(3) . . yes
O4 C19 1.444(3) . . yes
N1 C1 1.349(3) . . yes
N1 C2 1.398(3) . . yes
N2 N3 1.354(3) . . yes
N2 C1 1.427(2) . . yes
N2 C8 1.376(2) . . yes
N3 C10 1.339(2) . . yes
N1 H1 0.94(3) . . no
C2 C3 1.391(3) . . no
C2 C7 1.399(3) . . no
C3 C4 1.380(3) . . no
C4 C5 1.380(3) . . no
C5 C6 1.359(3) . . no
C6 C7 1.403(3) . . no
C7 C8 1.441(3) . . no
C8 C9 1.383(3) . . no
C9 C10 1.416(3) . . no
C9 C11 1.500(2) . . no
C11 C12 1.485(3) . . no
C12 C17 1.393(3) . . no
C12 C13 1.392(3) . . no
C13 C14 1.387(4) . . no
C14 C15 1.377(4) . . no
C15 C16 1.380(5) . . no
C16 C17 1.382(4) . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C6 H6 0.9300 . . no
C13 H13 0.9300 . . no
C14 H14 0.9300 . . no
C15 H15 0.9300 . . no
C16 H16 0.9300 . . no
C17 H17 0.9300 . . no
C18 H18A 0.9600 . . no
C18 H18B 0.9600 . . no
C18 H18C 0.9600 . . no
C19 H19A 0.9600 . . no
C19 H19B 0.9600 . . no
C19 H19C 0.9600 . . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 O4 107.50(9) . . . yes
O3 P1 O5 116.73(9) . . . yes
O3 P1 C10 101.74(9) . . . yes
O4 P1 O5 109.75(9) . . . yes
O4 P1 C10 107.48(9) . . . yes
O5 P1 C10 113.01(10) . . . yes
P1 O3 C18 118.83(14) . . . yes
P1 O4 C19 121.62(18) . . . yes
C1 N1 C2 126.33(17) . . . yes
N3 N2 C1 120.18(15) . . . yes
N3 N2 C8 113.51(15) . . . yes
C1 N2 C8 126.30(17) . . . yes
N2 N3 C10 103.79(15) . . . yes
C1 N1 H1 114.7(16) . . . no
C2 N1 H1 119.0(16) . . . no
O1 C1 N1 125.90(17) . . . yes
O1 C1 N2 121.92(18) . . . yes
N1 C1 N2 112.18(16) . . . yes
N1 C2 C3 119.26(17) . . . yes
C3 C2 C7 120.58(18) . . . no
N1 C2 C7 120.2(2) . . . yes
C2 C3 C4 120.02(19) . . . no
C3 C4 C5 118.4(2) . . . no
F1 C5 C6 118.64(17) . . . yes
F1 C5 C4 117.9(2) . . . yes
C4 C5 C6 123.4(2) . . . no
C5 C6 C7 118.67(17) . . . no
C2 C7 C6 118.92(18) . . . no
C6 C7 C8 124.14(17) . . . no
C2 C7 C8 116.92(17) . . . no
N2 C8 C9 105.44(16) . . . yes
N2 C8 C7 118.09(16) . . . yes
C7 C8 C9 136.39(16) . . . no
C8 C9 C11 130.40(17) . . . no
C8 C9 C10 105.08(15) . . . no
C10 C9 C11 124.39(16) . . . no
N3 C10 C9 112.17(17) . . . yes
P1 C10 C9 126.60(14) . . . yes
P1 C10 N3 121.22(15) . . . yes
O2 C11 C9 118.89(18) . . . yes
O2 C11 C12 121.86(17) . . . yes
C9 C11 C12 119.21(17) . . . no
C11 C12 C13 121.51(17) . . . no
C13 C12 C17 119.5(2) . . . no
C11 C12 C17 119.0(2) . . . no
C12 C13 C14 119.83(19) . . . no
C13 C14 C15 120.1(2) . . . no
C14 C15 C16 120.5(3) . . . no
C15 C16 C17 119.9(2) . . . no
C12 C17 C16 120.2(2) . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 121.00 . . . no
C5 C4 H4 121.00 . . . no
C5 C6 H6 121.00 . . . no
C7 C6 H6 121.00 . . . no
C12 C13 H13 120.00 . . . no
C14 C13 H13 120.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C14 C15 H15 120.00 . . . no
C16 C15 H15 120.00 . . . no
C15 C16 H16 120.00 . . . no
C17 C16 H16 120.00 . . . no
C12 C17 H17 120.00 . . . no
C16 C17 H17 120.00 . . . no
O3 C18 H18A 109.00 . . . no
O3 C18 H18B 109.00 . . . no
O3 C18 H18C 109.00 . . . no
H18A C18 H18B 109.00 . . . no
H18A C18 H18C 109.00 . . . no
H18B C18 H18C 109.00 . . . no
O4 C19 H19A 109.00 . . . no
O4 C19 H19B 109.00 . . . no
O4 C19 H19C 109.00 . . . no
H19A C19 H19B 109.00 . . . no
H19A C19 H19C 109.00 . . . no
H19B C19 H19C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 P1 O3 C18 -67.11(18) . . . . no
O5 P1 O3 C18 56.6(2) . . . . no
C10 P1 O3 C18 -179.89(17) . . . . no
O3 P1 O4 C19 -49.4(2) . . . . no
O5 P1 O4 C19 -177.3(2) . . . . no
C10 P1 O4 C19 59.4(2) . . . . no
O3 P1 C10 C9 -161.90(17) . . . . no
O4 P1 C10 C9 85.31(18) . . . . no
O5 P1 C10 C9 -35.9(2) . . . . no
O4 P1 C10 N3 -93.41(17) . . . . no
O5 P1 C10 N3 145.35(16) . . . . no
O3 P1 C10 N3 19.38(18) . . . . no
C2 N1 C1 N2 0.5(3) . . . . no
C2 N1 C1 O1 179.6(2) . . . . no
C1 N1 C2 C3 -178.9(2) . . . . no
C1 N1 C2 C7 0.4(3) . . . . no
N3 N2 C1 O1 -1.8(3) . . . . no
C8 N2 C1 N1 -1.3(3) . . . . no
C8 N2 C1 O1 179.58(19) . . . . no
N3 N2 C1 N1 177.32(17) . . . . no
N3 N2 C8 C7 -177.67(16) . . . . no
C1 N2 N3 C10 -177.96(17) . . . . no
C8 N2 N3 C10 0.8(2) . . . . no
C1 N2 C8 C9 178.27(17) . . . . no
C1 N2 C8 C7 1.0(3) . . . . no
N3 N2 C8 C9 -0.4(2) . . . . no
N2 N3 C10 P1 178.01(13) . . . . no
N2 N3 C10 C9 -0.9(2) . . . . no
C7 C2 C3 C4 0.8(4) . . . . no
N1 C2 C3 C4 -179.9(2) . . . . no
C3 C2 C7 C8 178.6(2) . . . . no
C3 C2 C7 C6 -0.1(3) . . . . no
N1 C2 C7 C6 -179.4(2) . . . . no
N1 C2 C7 C8 -0.7(3) . . . . no
C2 C3 C4 C5 -0.7(4) . . . . no
C3 C4 C5 F1 -178.8(2) . . . . no
C3 C4 C5 C6 -0.3(4) . . . . no
F1 C5 C6 C7 179.6(2) . . . . no
C4 C5 C6 C7 1.0(4) . . . . no
C5 C6 C7 C2 -0.8(3) . . . . no
C5 C6 C7 C8 -179.4(2) . . . . no
C6 C7 C8 N2 178.64(19) . . . . no
C6 C7 C8 C9 2.5(4) . . . . no
C2 C7 C8 N2 0.1(3) . . . . no
C2 C7 C8 C9 -176.1(2) . . . . no
N2 C8 C9 C10 -0.2(2) . . . . no
N2 C8 C9 C11 -176.04(18) . . . . no
C7 C8 C9 C10 176.4(2) . . . . no
C7 C8 C9 C11 0.5(4) . . . . no
C8 C9 C10 N3 0.7(2) . . . . no
C11 C9 C10 P1 -2.0(3) . . . . no
C11 C9 C10 N3 176.87(17) . . . . no
C8 C9 C11 O2 119.4(2) . . . . no
C8 C9 C11 C12 -62.9(3) . . . . no
C10 C9 C11 O2 -55.8(3) . . . . no
C10 C9 C11 C12 121.9(2) . . . . no
C8 C9 C10 P1 -178.14(14) . . . . no
O2 C11 C12 C13 161.0(2) . . . . no
O2 C11 C12 C17 -16.9(3) . . . . no
C9 C11 C12 C13 -16.7(3) . . . . no
C9 C11 C12 C17 165.48(19) . . . . no
C11 C12 C13 C14 -176.6(2) . . . . no
C17 C12 C13 C14 1.3(3) . . . . no
C11 C12 C17 C16 177.0(2) . . . . no
C13 C12 C17 C16 -0.9(4) . . . . no
C12 C13 C14 C15 -0.1(4) . . . . no
C13 C14 C15 C16 -1.5(4) . . . . no
C14 C15 C16 C17 1.9(4) . . . . no
C15 C16 C17 C12 -0.7(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
P1 O2 3.3576(18) . . no
P1 H1 3.12(3) . 1_665 no
F1 C6 3.329(3) . 2_657 no
F1 C15 3.281(3) . 2_667 no
F1 C16 3.287(3) . 2_667 no
F1 H15 2.7500 . 2_667 no
F1 H16 2.7800 . 2_667 no
O1 N3 2.750(2) . . no
O1 C13 3.397(3) . 2_656 no
O2 O5 3.196(2) . . no
O2 P1 3.3576(18) . . no
O2 C4 3.283(3) . 2_657 no
O3 N3 2.859(2) . . no
O3 C19 3.366(3) . 2_756 no
O4 C14 3.315(3) . 1_655 no
O5 O2 3.196(2) . . no
O5 C11 3.195(3) . . no
O5 N1 2.797(2) . 1_665 no
O5 C18 3.417(3) . 2_766 no
O5 C3 3.302(3) . 1_665 no
O1 H18B 2.7800 . 2_756 no
O1 H13 2.5100 . 2_656 no
O2 H17 2.6400 . 2_767 no
O2 H17 2.5600 . . no
O2 H4 2.6500 . 2_657 no
O3 H19B 2.7100 . . no
O3 H19B 2.8900 . 2_756 no
O4 H18B 2.8200 . . no
O4 H14 2.7300 . 1_655 no
O5 H3 2.5800 . 1_665 no
O5 H18C 2.8900 . . no
O5 H1 1.88(3) . 1_665 no
O5 H18C 2.8100 . 2_766 no
N1 O5 2.797(2) . 1_445 no
N3 O1 2.750(2) . . no
N3 O3 2.859(2) . . no
N3 C1 3.292(3) . 2_656 no
N3 H19B 2.7000 . 2_756 no
C1 N3 3.292(3) . 2_656 no
C3 O5 3.302(3) . 1_445 no
C4 O2 3.283(3) . 2_657 no
C4 C17 3.552(4) . 1_445 no
C5 C6 3.401(4) . 2_657 no
C6 C13 3.523(3) . . no
C6 C11 3.401(3) . . no
C6 C12 3.382(3) . . no
C6 C5 3.401(4) . 2_657 no
C6 C6 3.443(3) . 2_657 no
C6 F1 3.329(3) . 2_657 no
C7 C19 3.600(4) . 1_455 no
C8 C13 3.439(3) . . no
C11 C6 3.401(3) . . no
C11 O5 3.195(3) . . no
C12 C6 3.382(3) . . no
C13 C6 3.523(3) . . no
C13 C8 3.439(3) . . no
C13 C18 3.358(3) . 2_766 no
C13 O1 3.397(3) . 2_656 no
C14 C18 3.565(4) . 2_766 no
C14 O4 3.315(3) . 1_455 no
C15 C16 3.520(4) . 2_667 no
C15 F1 3.281(3) . 2_667 no
C16 C16 3.569(5) . 2_667 no
C16 F1 3.287(3) . 2_667 no
C16 C15 3.520(4) . 2_667 no
C17 C4 3.552(4) . 1_665 no
C18 O5 3.417(3) . 2_766 no
C18 C14 3.565(4) . 2_766 no
C18 C13 3.358(3) . 2_766 no
C19 O3 3.366(3) . 2_756 no
C19 C7 3.600(4) . 1_655 no
C2 H19A 2.9800 . 1_455 no
C6 H19A 2.8000 . 1_455 no
C7 H19A 2.7000 . 1_455 no
C8 H13 2.9400 . . no
C9 H13 2.6300 . . no
C9 H6 3.0200 . . no
C10 H19C 2.8600 . . no
C11 H6 2.7900 . . no
C12 H6 2.6200 . . no
C13 H6 3.0000 . . no
C13 H18C 2.8900 . 2_766 no
C16 H4 3.0300 . 1_665 no
C17 H4 2.8100 . 1_665 no
C18 H19B 3.1000 . . no
H1 P1 3.12(3) . 1_445 no
H1 O5 1.88(3) . 1_445 no
H1 H3 2.3800 . . no
H3 O5 2.5800 . 1_445 no
H3 H1 2.3800 . . no
H4 C16 3.0300 . 1_445 no
H4 C17 2.8100 . 1_445 no
H4 H17 2.5600 . 1_445 no
H4 O2 2.6500 . 2_657 no
H6 C9 3.0200 . . no
H6 C11 2.7900 . . no
H6 C12 2.6200 . . no
H6 C13 3.0000 . . no
H13 C8 2.9400 . . no
H13 C9 2.6300 . . no
H13 O1 2.5100 . 2_656 no
H14 O4 2.7300 . 1_455 no
H15 F1 2.7500 . 2_667 no
H16 F1 2.7800 . 2_667 no
H17 O2 2.5600 . . no
H17 H4 2.5600 . 1_665 no
H17 O2 2.6400 . 2_767 no
H18B O4 2.8200 . . no
H18B O1 2.7800 . 2_756 no
H18C O5 2.8900 . . no
H18C O5 2.8100 . 2_766 no
H18C C13 2.8900 . 2_766 no
H19A C2 2.9800 . 1_655 no
H19A C6 2.8000 . 1_655 no
H19A C7 2.7000 . 1_655 no
H19B O3 2.7100 . . no
H19B C18 3.1000 . . no
H19B O3 2.8900 . 2_756 no
H19B N3 2.7000 . 2_756 no
H19C C10 2.8600 . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O5 0.94(3) 1.88(3) 2.797(2) 164(2) 1_445 yes
C3 H3 O5 0.9300 2.5800 3.302(3) 135.00 1_445 yes
C13 H13 O1 0.9300 2.5100 3.397(3) 160.00 2_656 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
